Poorly maintained sidewalks pose considerable accessibility challenges for people with mobility impairments. Despite comprehensive civil rights legislation of Americans with Disabilities Act, many city streets and sidewalks in the U.S. remain inaccessible.The problem is not just that sidewalk accessibility fundamentally affects where and how people travel in cities, but also that there are few, if any, mechanisms to determine accessible areas of a city a priori.To address this problem, my Ph.D. dissertation introduces and evaluates new scalable methods for collecting data about street-level accessibility using a combination of crowdsourcing, automated methods, and Google Street View (GSV). My dissertation has four research threads. First, we conduct a formative interview study to establish a better understanding of how people with mobility impairments currently assess accessibility in the built environment and the role of emerging location-based technologies therein. The study uncovers the existing methods for assessing accessibility of physical environment and identify useful features of future assistive technologies. Second, we develop and evaluate scalable crowdsourced accessibility data collection methods. We show that paid crowd workers recruited from an online labor marketplace can find and label accessibility attributes in GSV with accuracy of 81%. This accuracy improves to 93% with quality control mechanisms such as majority vote. Third, we design a system that combines crowdsourcing and automated methods to increase data collection efficiency. Our work shows that by combining crowdsourcing and automated methods, we can increase data collection efficiency by 13% without sacrificing accuracy. Fourth, we develop and deploy a web tool that lets volunteers to help us collect the street-level accessibility data from Washington, D.C.As of writing this dissertation, we have collected the accessibility data from 20% of the streets in D.C. We conduct a preliminary evaluation on how the said web tool is used.Finally, we implement proof-of-concept accessibility-aware applications with accessibility data collected with the help of volunteers.My dissertation contributes to the accessibility, computer science, and HCI communities by: (i) extending the knowledge of how people with mobility impairments interact with technology to navigate in cities; (ii) introducing the first work that demonstrates that GSV is a viable source for learning about the accessibility of the physical world; (iii) introducing the first method that combines crowdsourcing and automated methods to remotely collect accessibility information; (iv) deploying interactive web tools that allow volunteers to help populate the largest dataset about street-level accessibility of the world; and (v) demonstrating accessibility-aware applications that empower people with mobility impairments.